I know what you’re thinking—so what? You never know something is the perfect fit until you try it on.

Well, yes. Proper Cloth is well aware of that challenge, and has anticipated how to get around that objection. Every first shirt a customer orders can be further customized or returned for free, even if it’s the consumer who picked the wrong sizing.

“It makes every first shirt a test shirt,” he says. “We’re more than happy to lose a little bit on the first shirt to get them satisfied and stoked on the fit.”

Let’s back track. Skerritt says he felt firsthand the pain of trying to find the right business attire while working in the corporate world. “The process was go to the mall, try on stuff, and try to find something you like,” he says. “It’s totally frustrating and annoying, and you end up making a lot of compromises just to get it over with.”

While at MIT Sloan School of Management, Skerritt knew he wanted to start his own company upon graduating, he says. And the inspiration came while he was on an internship in Asia and had his first experience with custom shirt ordering.

“It seemed like the kind of offering that could be very interesting if it was rolled up into a really clean, customer service oriented, e-commerce experience,” he says.

Skerritt started working on the business in April 2008 while still in school, and had the site live that October. Proper Cloth now offers a wide array of shirt collections men can choose from, or the ability to custom design personal shirts from the ground up. Consumers select fabric, collar and cuff shape and style, accents, buttons, monograms, pockets, and more through the company’s online interface.

As far as the fit goes, customers can pick the collar size, sleeve length, and type of fit (classic, slim, or super slim). For those who are a bit more clueless on this front, Proper Cloth offers a survey asking customers questions about things like their current shirt sizes, “belly situation” (six-pack abs or pot belly, for example), height, and weight, to generate the right size for them. “Some guys have a lot of experience and others have a lot of specific desires,” Skerritt says. “Others have no clue. We try to not overwhelm the novice customer but still satisfy the expert.”

Shirts range from $89 to $200+, with the average shirt costing around $130, he says. The company has hit profitability, and some weeks has sold 300 shirts, Skerritt says. Customers typically get their orders within two to three weeks of designing and purchasing them on the site, which works with a production facility in Malaysia.

Proper Cloth, which operates out of Polaris Venture Partners’ Dogpatch Labs in New York, is keeping it lean with just two employees working alongside Skerritt. The company has raised about $150,000 from family and friends, but could raise a bigger funding round to help it better scale, Skerritt says. And as consumers become more comfortable buying almost anything online, more competitors are bound to be attracted to the space. Proper Cloth certainly isn’t the only consumer Internet company aimed at men’s clothing—Vancouver, BC-based Indochino raised $4 million last month to expand its business that offers tailored suits online.

Ultimately, Proper Cloth is looking to create an e-commerce, custom shirt experience akin to some of the top retailers online, Skerritt says. “There should be a Zappos-style simple way to buy custom shirts online,” he says. “It doesn’t need to be about the custom part, but getting exactly what you want with minimal hassle.”

T-shirts range from $ 89 to $ 200 +, with the average shirt costs about $ 130. There are less expensive?

el dorko

I’ve purchased a few Proper Cloth shirts and while the customer service was great and the fit was eventually perfect – they cannot compete with the fabric selection and quality of J Hilburn. Sorry Seph but I converted.

http://www.bespokefitshirt.com/ John

Better than Propercloth, I ordered from Bespoke Fit Shirt….

Joy Yung

Once i did shopping of custom dress shirts from one of the online customize store http://www.nattyshirts.us/ and it was really nice custom dress shirts.

led spotlight Melbourne

I ‘ve purchased a few Proper Cloth shirts and while the customer service was great and the fit was eventually perfect –